Organically functionalized carbon nanocapsule

ABSTRACT

An organically functionalized carbon nanocapsule is provided. The organically-functionalized carbon nanocapsule includes a hollow carbon nanocapsule having a purity of at least more than 50% and a surface and at least one kind of organic functional groups bonded thereon and uniformly distributed over the surface thereof. The organically-functionalized carbon nanocapsule is of the following formula: F(-E)n, in which F is the carbon nanocapsule, E is the organic functional group, and n is the number of the organic functional group. By functionalization of high-purity carbon nanocapsules, the application thereof is expanded.

This application is a Continuation-In-Part of U.S. patent applicationSer. No. 10/606,965, filed Jun. 27, 2003 now abandoned, and entitled“organically functionalized carbon nanocapsule”.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to carbon nanocapsules, and in particular tofunctionalized carbon nanocapsules.

2. Description of the Related Art

A carbon nanocapsule is a polyhedral carbon cluster constituted bymultiple graphite layers having a balls-within-a ball structure. Thediameter of a carbon nanocapsule is about 3-100 nm. There are two typesof carbon nanocapsules: hollow and metal-filled. The center of a hollowcarbon nanocapsule is, of course, hollow, while that of a metal-fillednanocapsule is filled with metals, metal oxides, metal carbides, oralloys.

Carbon nanocapsules were first discovered with carbon nanotubes in 1991,in the process of producing carbon nanotubes. Owing to the strong vander Waals force between carbon nanocapsules and carbon nanotubes, it isnot easy to isolate carbon nanocapsules from the carbon nanotubes. Inaddition, the amount of carbon nanocapsules produced with carbonnanotubes is only enough for structural observation under electronmicroscope, thus the application thereof is obstructed.

By continuous research, processes producing high-purity hollow carbonnanocapsules as well as magnetic metal-filled carbon nanocapsules havebeen developed. (Please refer to U.S. patent application Ser. Nos.10/255,669 and 10/329,333) With their special fullerene structure andoptoelectronic properties, carbon nanocapsules can be utilized invarious fields such as medicine (medical grade active carbon), light andheat absorption, electromagnetic shielding, organic light emittingmaterials, solar energy receivers, catalysts, sensors, carbon electrodesin lithium batteries, nanoscale composite materials with thermalconductivity and special electrical properties, and nanoscale carbonpowder for printing. However, owing to the non-solubility of carbonnanocapsules, the related application is limited and insufficient.

BRIEF SUMMARY OF THE INVENTION

One embodiment of the invention is to functionalize carbon nanocapsulesto prepare organically-functionalized carbon nanocapsules, therebyexpanding the application thereof.

One embodiment of the invention provides an organically-functionalizedcarbon nanocapsule. The organically-functionalized carbon nanocapsuleincludes a hollow carbon nanocapsule having a purity of at least morethan 50% and a surface and at least one kind of organic functionalgroups bonded thereon and uniformly distributed over the surfacethereof. The organically-functionalized carbon nanocapsule is of thefollowing formula: F(-E)n, in which F is the carbon nanocapsule, E isthe organic functional group, and n is the number of the organicfunctional group.

A detailed description is given in the following embodiments withreference to the accompanying drawings.

BRIEF DESCRIPTION OF THE DRAWINGS

The invention can be more fully understood by reading the subsequentdetailed description and examples with references made to theaccompanying drawing, wherein:

FIG. 1 illustrates the functionalization of carbon nanocapsulesinvolving a redox reaction according to an embodiment of the invention.

FIG. 2 a illustrates the functionalization of carbon nanocapsulesinvolving a cycloaddition reaction in the example 2a of the invention.

FIG. 2 b illustrates the functionalization of carbon nanocapsulesinvolving a radical addition reaction in the example 2b of theinvention.

DETAILED DESCRIPTION OF THE INVENTION

The following description is of the best-contemplated mode of carryingout the invention. This description is made for the purpose ofillustrating the general principles of the invention and should not betaken in a limiting sense. The scope of the invention is best determinedby reference to the appended claims.

The carbon nanocapsule is a polyhedral carbon cluster constitutingmultiple graphite layers having a balls-within-a ball structure, and thediameter of the carbon nanocapsule is 3-100 nm.

The carbon nanocapsule is a hollow carbon nanocapsule or a metal-filledcarbon nanocapsule filled with metals, metal oxides, metal carbides, oralloys.

Before preparing organically-functionalized carbon nanocapsules,high-purity carbon nanocapsules, for example, at least more than 50%must be prepared first, by the preparation method described, forexample, in the above-mentioned references. The carbon nanocapsuleobtained is a polyhedral carbon cluster constituting multiple graphitelayers having a balls-within-a ball structure, wherein the diameter of acarbon nanocapsule is 3-100 nm. The carbon nanocapsules for preparationof organically-functionalized carbon nanocapsules can be hollow orfilled with metals, metal oxides, metal carbides, or alloys.

By functionalization of the carbon nanocapsule, at least one kind offunctional groups is bonded on the carbon nanocapsule and uniformlydistributed over the surface of the carbon nanocapsule, therebyincreasing its reactivity. By functionalization with differentfunctional groups, the reactive variety thereof is enriched, and therebythe application is expanded.

The functionalizing methods of carbon nanocapsules applied in theinvention are analogic to those of carbon 60. However, owing to therelatively greater size of carbon nanocapsules, the nano-dispersingtechnique is important for the control of chemical modifying effects. Inaddition, carbon nanocapsules have different optical, electrical, andmagnetic properties from carbon nanotubes and carbon 60, thus theorganically-functionalized carbon nanocapsules have distinctapplications.

The carbon nanocapsules can be functionalized by a redox reaction,cycloaddition reaction, or a radical addition reaction. Specifically,the organic functional groups are bonded thereon and uniformlydistributed over the surface thereof.

In the redox reaction, the carbon nanocapsule is reacted with a strongoxidant, for example, H₂SO₄+HNO₃, OSO₄, KMnO₄ or O₃, to oxidize thesurface carbon layer of the carbon nanocapsule and form a functionalgroup, for example, —OH, —C═O, —CHO or —COOH, on the carbon nanocapsule.

In the cycloaddition reaction, the carbon nanocapsule is functionalizedvia the double bonds on the surface of the carbon nanocapsule. Compoundssuch as aniline, N,N-dimethylaniline, CH₂O (aldehyde), CH₃NHCH₂COOH(N-substituted glycine derivative), or (CHCl₃+KOH), are reacted with thecarbon nanocapsule to form functional groups, for example, —NHAr,—N⁺(CH₃)₂Ar, ═CCl₂ or amino groups, on the carbon nanocapsule.

In the radical addition reaction, the carbon nanocapsule isfunctionalized via the double bonds on the surface of the carbonnanocapsule. The carbon nanocapsule is reacted with a free-radicalinitiator or molecules capable of producing radicals, for example,K₂S₂O₈, H₂O₂, methylmethacrylate, or azobis-isobutyronitrile (AIBN), tobond functional groups, for example, —OSO₃ ⁻, —OH, —C(CH₃)₂COOCH₃ or—C(CH₃)₂CN on the carbon nanocapsule.

In the above three kinds of preparation methods, the method involvingredox reaction is quite different from the conventional preparationmethods of fullerene derivatives. In the redox reaction, strong oxidantsare applied to oxidize the surface layers of carbon nanocapsules to formfunctional groups, for example, —OH, —C═O, —CHO or —COOH, on the surfaceof carbon nanocapsules. The functionalized carbon nanocapsules are thenable to react with any other compounds to form more complicatedfunctionalized carbon nanocapsules. In the preparation methods offullerene derivatives, however, oxidants are not applied because of thedifferent structure of fullerene molecules. Strong oxidantsfunctionalize molecules by breaking bonds between carbon atoms, whichcause damage to a fullerene structure, while still applicable on acarbon nanocapsule by virtue of the multiple-graphite-layer structure.

In addition, U.S. Pat. No. 5,177,248 and U.S. Pat. No. 5,294,732incorporated herein by reference describe other preparation methods oforganically-functionalized carbon nanocapsules.

By functionalization of carbon nanocapsule, anorganically-functionalized carbon nanocapsule is provided, comprising ahollow carbon nanocapsule having a purity of at least more than 50% anda surface and at least one kind of organic functional groups bondedthereon and uniformly distributed over the surface thereof, wherein theorganically-functionalized carbon nanocapsule is of the followingformula: F(-E)n, in which F is the carbon nanocapsule, E is the organicfunctional group, and n is the number of the organic functional group,for example, n is 1-100,000. Additionally, the carbon nanocapsule has anaspect ratio of about 1-5 or 1-2.

In the organically-functionalized carbon nanocapsule, each E isindependently E₁, E₂, E₃, E₄ or E₅, in which each E₁, independently, isY₁,Y₂-amino, (Y₁,Y₂-alkyl)amino, Y₁,Y₂-ethylendiamino,(dihydroxymethyl)alkylamino, (X₁,X₃-aryl)amino, or X₁,X₃-aryloxy, eachE₂, independently, is Y₁,Y₂-alkoxy, (Y₁,Y₂-amino)alkoxy,(Y₁,Y₂,Y₃-aryl)oxy, (dihydroxyalkyl)aryloxy, (Y₁,Y₂,Y₃-alkyl)amino,(Y₁,Y₂,Y₃-aryl)amino, or dihydroxyalkylamino, each E₃, independently, isY₁,Y₂,Y₃-alkoxy, (trihydroxyalkyl)alkoxy, (trihydroxyalkyl)alkylamino,(dicarboxyalkyl)amino, (Y₁,Y₂,Y₃-alkyl)thio, (X₁,X₂-aryl)thio,(Y₁,Y₂-alkyl)thio, (dihydroxyalkyl)thio, Y₁,Y₂-dioxoalkyl, each E₄,independently, is ((glycosidyl)oxoheteroaryl)amino,((glycosidyl)oxoaryl)amino, (X₁,X₂,X₃-heteroaryl)amino,(X₁-diarylketone)amino, (X,X₁-oxoaryl)amino, (X,X₁-dioxoaryl)amino,(Y₁-alkyl,Y₂-alkyldioxoheteroaryl)amino,(Y₁-alkyl,Y₂-alkyldioxoaryl)amino,(di(Y₁,Y₂-methyl)dioxoheteroaryl)amino,(di(Y₁,Y₂-methyl)dioxoaryl)amino, ((glycosidyl)heteroaryl)amino,((glycosidyl)aryl)amino, ((carboxylacetylalkyl)oxoheteroaryl)amino,((carboxylacetylalkyl)oxoaryl)amino,((isopropylaminohydroxyalkoxy)aryl)amino, or (X₁,X₂,X₃-alkylaryl)amino,and each E₅, independently, is (X₁,X₂,X₃-heteroaryl)oxy,(isopropylaminohydroxyalkyl)aryloxy, (X₁,X₂,X₃ -oxoheteroaryl)oxy,(X₁,X₂,X₃-oxoaryl)oxy, (X₁,Y₁-oxoheteroaryl)oxy, (X₁-diarylketone)oxy,(X,X₁-oxoaryl)oxy, (X,X₂-dioxoaryl)oxy, (Y₁,Y₂,di-aminodihydroxy)alkyl,(X₁,X₂-heteroaryl)thio, ((tricarboxylalkyl)ethylendiamino)alkoxy,(X₁,X₂-oxoaryl)thio, (X₁,X₂-dioxoaryl)thio, (glycosidylheteroaryl)thio,(glycosidylaryl)thio, Y₁-alkyl(thiocarbonyl)thio,Y₁,Y₂-alkyl(thiocarbonyl)thio, Y₁,Y₂,Y₃-alkyl(thiocarbonyl)thio,(Y₁,Y₂-aminothiocarbonyl)thio, (pyranosyl)thio, cysteinyl, tyrosinyl,(phenylalanyl)amino, (dicarboxyalkyl)thio, (aminoaryl)₁₋₂₀ amino, or(pyranosyl)amino.

Each X, independently, is halide, each of X₁ and X₂, independently, is—H, —Y₁, —O—Y₁, —S—Y₁, —NH—Y₁, —CO—O—Y₁, —O—CO—Y₁, —CO—NH—Y₁, —CO—NY₁Y₂,—NH—CO—Y₁, —SO₂—Y₁, —CHY₁Y₂, or —NY₁Y₂, and each X₃, independently, is—Y₁, —O—Y₁, —S—Y₁, —NH—Y₁, —CO—O—Y₁, —O—CO—Y₁, —CO—NH—Y₁, —CO—NY₁Y₂,—NH—CO—Y₁, —SO₂—Y₁, —CHY₁Y₂ or —NY₁Y₂;

Each X, independently, is halide, each of X₁ and X₂, independently, is—H, —Y₁, —O—Y₁, —S—Y₁, —NH—Y₁, —CO—O—Y₁, —O—CO—Y₁, —CO—NH—Y₁, —CO—NY₁Y₂,—NH—CO—Y₁, —SO₂—Y₁, —CHY₁Y₂, or —NY₁Y₂, and each X₃, independently, is—Y₁, —O—Y₁, —S—Y₁, —NH—Y₁, —CO—O—Y₁, —O—CO—Y₁, —CO—NH—Y₁, —CO—NY₁Y₂,—NH—CO—Y₁, —SO₂—Y₁, —CHY₁Y₂ or —NY₁Y₂.

Each of Y₁, Y₂ and Y₃, independently, is —B-Z.

Each B, independently, is —R_(a)—O—[Si(CH₃)₂—O—]₁₋₁₀₀, C₁₋₂₀₀₀ alkyl,C₆₋₄₀ aryl, C₇₋₆₀ alkylaryl, C₇₋₆₀ arylalkyl, (C₁₋₃₀ alkyl ether)₁₋₁₀₀,(C₆₋₄₀ aryl ether)₁₋₁₀₀, (C₇₋₆₀ alkylaryl ether)₁₋₁₀₀, (C₇₋₆₀ arylalkylether)₁₋₁₀₀, (C₁₋₃₀ alkyl thioether)₁₋₁₀₀(C₆₋₄₀ aryl thioether)₁₋₁₀₀,(C₇₋₆₀ alkylaryl thioether)₁₋₁₀₀, (C₇₋₆₀ arylalkyl thioether)₁₋₁₀₀,(C₂₋₅₀ alkyl ester)₁₋₁₀₀, (C₇₋₆₀ aryl ester)₁₋₁₀₀, (C₈₋₇₀ alkylarylester)₁₋₁₀₀, (C₈₋₇₀ arylalkyl ester)₁₋₁₀₀, —R—CO—O—(C₁₋₃₀ alkylether)₁₋₁₀₀, —R—CO—O—(C₆₋₄₀ aryl ether)₁₋₁₀₀, —R—CO—O—(C₇₋₆₀ alkylarylether)₁₋₁₀₀, —R—CO—O—(C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, (C₄₋₅₀ alkylurethane)₁₋₁₀₀ (C₁₄₋₆₀ aryl urethane)₁₋₁₀₀, (C₁₀₋₈₀ alkylarylurethane)₁₋₁₀₀ (C₁₀₋₈₀ arylalkyl urethane)₁₋₁₀₀, (C₅S₅₀ alkylurea)₁₋₁₀₀, (C₁₄₋₆₀ aryl urea)₁₋₁₀₀ (C₁₀₋₈₀ alkylaryl urea)₁₋₁₀₀,(C₁₀₋₈₀ arylalkyl urea)₁₋₁₀₀, (C₂₋₅₀ alkyl amide)₁₋₁₀₀, (C₇₋₆₀ arylamide)₁₋₁₀₀, (C₈₋₇₀ alkylaryl amide)₁₋₁₀₀ (C₈₋₇₀ arylalkyl amide)₁₋₁₀₀,(C₃₋₃₀ alkyl anhydride)₁₋₁₀₀, (C₈₋₅₀ aryl anhydride)₁₋₁₀₀, (C₉₋₆₀alkylaryl anhydride)₁₋₁₀₀, (C₉₋₆₀ arylalkyl anhydride)₁₋₁₀₀, (C₂₋₃₀alkyl carbonate)₁₋₁₀₀, (C₇₋₅₀ aryl carbonate)₁₋₁₀₀, (C₈₋₆₀ alkylarylcarbonate)₁₋₁₀₀, (C₈₋₆₀ arylalkyl carbonate)₁₋₁₀₀, —R₁, —O—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ aryl ether, C₇₋₆₀ alkylarylether, or C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, —R₁—O—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O(C₂₋₅₀ alkyl ester, C₇₋₆₀ aryl ester, C₈₋₇₀ alkylarylester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀, —R₁—C—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ aryl ether, C₇₋₆₀ alkylarylether, or C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, —CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—,—R₁—O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—(C₂₋₅₀ alkyl ester, C₇₋₆₀ arylester, C₈₋₇₀ alkylaryl ester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀,—R₃—O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—, —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ aryl ether, C₇₋₆₀ alkylarylether, or C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₂₋₅₀ alkyl ester, C₇₋₆₀ aryl ester, C₈₋₇₀ alkylarylester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀, —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ aryl ether, C₇₋₆₀ alkylarylether, or C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, —CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—,—R₁—NH—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—(C₂₋₅₀ alkyl ester, C₇₋₆₀ arylester, C₈₋₇₀ alkylaryl ester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀,—R₃—O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—, —R₁—O—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—NH—(C₂₋₅₀ alkyl amide, C₇₋₆₀ aryl amide, C₈₋₇₀ alkylarylamide, or C₈₋₇₀ arylalkyl amide)₁₋₁₀₀, or —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)NH—CO—NH—(C₂₋₅₀ alkyl amide, C₇₋₆₀ aryl amide, C₈₋₇₀ alkylarylamide, or C₈₋₇₀ arylalkyl amide)₁₋₁₀₀.

Each Z, independently, is —C-D-, wherein each C, independently, is —R—,—R—Ar—, —Ar—R—, or —Ar—, and each D, independently, is —OH, —SH, —NH₂,—NHOH, —SO₃H, —OSO₃H, —COOH, —CONH₂, —CO—NH—NH₂, —CH(NH₂)—COOH, —P(OH)₃,—PO(OH)₂, —O—PO(OH)₂, —O—PO(OH)—O—PO(OH)₂, —O—PO(O—)—O—CH₂CH₂NH₃ ⁺,-glycoside, —OCH₃, —O—CH₂—(CHOH)₄—CH₂₄—CH, —O—CH₂—(CHOH)₂—CHOH,—C₆H₃(OH)₂, —NH₃ ⁺, —N⁺HR_(b)R_(c), or N⁺HR_(b)R_(c)R_(d), wherein eachof R, R₁, R₂, R₃, R_(a), R_(b), R_(c), and R_(d) independently, is C₁₋₃₀alkyl, each Ar, independently, is aryl.

EXAMPLE 1 Redox Reaction

FIG. 1 illustrates the functionalization of carbon nanocapsulesinvolving a redox reaction.

A reaction flask (1 L) was charged with carbon nanocapsules (1.0 g)dissolved in sulfuric acid/nitric acid (weight ratio=1:1). The mixturewas stirred by an ultrasonic cleaner for 10 mins, and then heated toabout 140° C. and refluxed for 2 hours. Afterwards, the mixture wascentrifuged to separate the carbon nanocapsules from the strong acid,rinsing the carbon nanocapsules thoroughly followed by severalcentrifuges, until the pH value of carbon nanocapsules approached 7. Thecarbon nanocapsules obtained were black with —COOH groups bondedthereon. By titration using NaOH, the concentration of the —COOH groupswas identified as 13 μmols/per gram carbon nanocapsules. The oxidizationof carbon nanocapsules resulted in damage of the surface carbon layers,which could be observed under a transmission electron microscope. Theorganically-functionalized carbon nanocapsules were soluble in water byvirtue of the COOH groups.

EXAMPLE 2 Cycloaddition Reaction Example 2a

FIG. 2 a illustrates the functionalization of carbon nanocapsulesinvolving a cycloaddition reaction in the example 2a.

A reaction flask (1 L) was charged with carbon nanocapsules (1.0 g)dissolved in a saturated DMF (dimethyl formamide) solution of aldehydeand N-substituted glycine derivative (molar ratio=1:1). The mixture wasthen stirred by an ultrasonic cleaner for 10 mins, and heated to about130° C. and refluxed for 120 hours. Afterwards, the mixture wascentrifuged to separate the carbon nanocapsules from the solution. Thereaction was as shown in FIG. 2 a, with a product soluble in chloroformor water.

Example 2b

FIG. 2 b illustrates the functionalization of carbon nanocapsulesinvolving a radical addition reaction in the example 2b.

A reaction flask (1 L) was charged with carbon nanocapsules (1.0 g)dissolved in N,N-dimethylaniline (500 ml). The mixture was then stirredby an untrasonic cleaner for 10 mins, heated, and refluxed for 12 hours.Afterwards, the mixture was centrifuged to separate the carbonnanocapsules from the solution. The reaction was as shown in FIG. 2 b,with a product soluble in water.

EXAMPLE 3 Radical Addition Reaction Example 3a

A reaction flask (IL) was charged with carbon nanocapsules (100 mg) andK₂S₂O₈ (120 mg) dissolved in water (500 ml). The solution mixture waspurged with N₂ prior to stirring and heating to 70° C. for 5 hours. Theproduct was black carbon nanocapsules with —OSO₃ ⁻ groups bondedthereon, easily soluble in water. The radical addition reaction wasobserved by the electron spin resonance spectrum (ESR), in which thesignal at g=2.0032, ΔH_(pp)=4.32 G represents the bonding of radicals.

Example 3b

A reaction flask (IL) was charged with carbon nanocapsules (100 mg) andmethylmethacrylate (25 ml) dissolved in toluene (250 ml). The solutionmixture was illuminated at room temperature to initiate radicalgeneration of methylmethacrylate, thereby reacting with the surfacedouble bonds of the carbon nanocapsules. The radical addition reactionwas observed by the electron spin resonance spectrum (ESR), in whichsignals at g=2.0033, ΔH_(pp)=8.56 G and g=2.0037, ΔH_(pp)=4.44 Grepresent the bonding of radicals.

While the invention has been described by way of example and in terms ofpreferred embodiment, it is to be understood that the invention is notlimited thereto. To the contrary, it is intended to cover variousmodifications and similar arrangements (as would be apparent to thoseskilled in the art). Therefore, the scope of the appended claims shouldbe accorded the broadest interpretation so as to encompass all suchmodifications and similar arrangements.

1. An organically-functionalized carbon nanocapsule, comprising: ahollow carbon nanocapsule of a polyhedral carbon cluster constitutingmultiple graphitic layers having a purity of at least more than 50% anda surface, wherein the carbon nanocapsule has an aspect ratio of about1-2; and at least one organic functional groups bonded thereon anduniformly distributed over the surface thereof, wherein theorganically-functionalized carbon nanocapsule is of the followingformula: F(-E)n, in which F is the carbon nanocapsule, E is the organicfunctional group, and n is the number of the organic functional group,wherein each E is independently E₁, E₂, E₃, E₄ or E₅, in which each E₁,independently, is Y₁,Y₂,-amino, (Y₁,Y₂-alkyl) amino, Y₁,Y₂-ethylenediamino, (dihydroxymethyl)alkylamino, (X₁,X₃-aryl)amino, orX₁,X₃-aryloxy; each E₂, independently, is Y₁,Y₂-alkoxy,(Y₁,Y₂-amino)alkoxy, (Y₁,Y₂,Y₃-aryl)oxy, (dihydroxyalkyl)aryloxy,(Y₁,Y₂,Y₃-alkyl)amino, (Y₁,Y₂,Y₃ -aryl)amino, or dihydroxyalkylamino;each E₃, independently, is Y₁,Y₂,Y₃ -alkoxy, (trihydroxyalkyl)alkoxy,(trihydroxyalkyl)alkylamino, (dicarboxyalkyl)amino, (Y₁,Y₂,Y₃-alkyl)thio, (X₁,X₂ -aryl)thio, (Y₁,Y₂ -alkyl)thio,(dihydroxyalkyl)thio, Y₁,Y₂ -dioxoalkyl; each E₄, independently, is((glycosidyl)oxoheteroaryl)amino, ((glycosidyl)oxoaryl)amino, (X₁,X₂,X₃-heteroaryl)amino, (X₁ -diarylketone)amino, (X,X₁ -oxoaryl)amino, (X,X₁-dioxoaryl) amino, (Y₁-alkyl, Y₂-alkyldioxoheteroaryl)amino, (Y₁-alkyl,Y₂ -alkyldioxoaryl)amino, (di(Y₁,Y₂ -methyl)dioxoheteroaryl)amino,(di(Y₁, Y₂ -methyl)dioxoaryl)amino, ((glycosidyl)heteroaryl)amino,((glycosidyl)aryl)amino, ((carboxylacetylalkyl)oxoheteroaryl)amino,((carboxylacetylalkyl)oxoaryl)amino,((isopropylaminohydroxyalkoxy)aryl)amino, or (X₁,X₂,X₃ -alkylaryl)amino;each E₅, independently, is (X₁,X₂,X₃-heteroaryl)oxy,(isopropylaminohydroxyalkyl)aryloxy, (X₁,X₂,X₃-oxoheteroaryl)oxy,(X₁,X₂,X₃-oxoaryl)oxy, (X₁,Y₁-oxoheteroaryl)oxy, (X₁-diarylketone)oxy,(X,X₁ -oxoaryl)oxy, (X₁,X₂ -dioxoaryl)oxy,(Y₁,Y₂,di-aminodihydroxy)alkyl, (X₁,X₂ -heteroaryl)thio,((tricarboxylalkyl)ethylenediamino)alkoxy, (X₁,X₂ -oxoaryl)thio, (X₁,X₂-dioxoaryl)thio, (glycosidylheteroaryl)thio, (glycosidylaryl)thio, Y₁-alkyl(thiocarbonyl)thio, Y₁,Y₂ -alkyl(thiocarbonyl)thio, Y₁,Y₂,Y₃-alkyl(thiocarbonyl)thio, (Y₁,Y₂ -aminothiocarbonyl)thio,(pyranosyl)thio, cysteinyl, tyrosinyl, (phenylalainyl)amino,(dicarboxyalkyl)thio, (aminoaryl)₁₋₂₀ amino, or (pyranosyl)amino; eachX, independently, is halide; each of X₁ and X₂, independently, is —H,—Y₁, —O—Y₁, —S—Y₁, —NH—Y₁, —CO—O—Y₁, —O—CO—Y₁, —CO—NH—Y₁, —CO—NY₁Y₂,—NH—CO—Y₁, —SO₂Y₁, —CHY₁Y₂, or —NY₁Y₂; each X₃, independently, is —Y₁,—O—Y₁, —S—Y₁, —NH—Y₁, —CO—O—Y₁, —O—CO—Y₁, —CO—NH —Y₁, —CO—NY₁Y₂,NH—CO—Y₁, —SO₂—Y₁, —CHY₁Y₂or —NY₁Y₂; each of Y₁, Y₂ and Y₃,independently, is —B—Z; each B, independently, is—R_(a)—O—[Si(CH₃)₂—O—]₁₋₁₀₀, C₁₋₂₀₀₀ alkyl, C₆₋₄₀ aryl, C₇₋₆₀ alkylaryl,C₇₋₆₀ arylalkyl, (C₁₋₃₀ alkyl ether)₁₋₁₀₀, (C₆₋₄₀ aryl ether)₁₋₁₀₀,(C₇₋₆₀ alkylaryl ether)₁₋₁₀₀, (C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, (C₁₋₃₀ alkylthioether)₁₋₁₀₀(C₆₋₄₀ aryl thioether)₁₋₁₀₀, (C₇₋₆₀ alkylarylthioether)₁₋₁₀₀, (C₇₋₆₀arylalkyl thioether)₁₋₁₀₀, (C₂₋₅₀ alkylester)₁₋₁₀₀, (C₇₋₆₀ aryl ester)₁₋₁₀₀, (C ₈₋₇₀ alkylaryl ester)₁₋₁₀₀,(C₈₋₇₀ arylalkyl ester)₁₋₁₀₀, —R—CO—O—(C₁₋₃₀ alkyl ether)₁₋₁₀₀,—R—CO—O—(C₆₋₄₀ aryl ether)₁₋₁₀₀, —R—CO—O—(C₇₋₆₀ alkylaryl ether)₁ ₋₁₀₀,—R—CO—O—(C₇₋₆₀ arylalkl ether)₁₋₁₀₀, (C₄₋₅₀ alkyl urethane)₁₋₁₀₀(C₁₄₋₆₀aryl urethane)₁₋₁₀₀, (C₁₀₋₈₀ alkylaryl urethane)₁₋₁₀₀ (C₁₀₋₈₀ arylalkylurethane)₁₋₁₀₀, (C₅₋₅₀ alkyl urea)₁₋₁₀₀, (C₁₄₋₆₀ aryl urea)₁₋₁₀₀(C_(10-λ)alkylaryl urea)₁₋₁₀₀, (C₁₀₋₈₀ arylalkyl urea) ₁₋₁₀₀, (C₂₋₅₀alkyl amide)₁₋₁₀₀, (C₇₋₆₀ aryl amide)₁₋₁₀₀, (C₈₋₇₀ alkylaryl amide)₁₋₁₀₀ (C₈₋₇₀ arylalkyl amide) ₁₋₁₀₀, (C₃₋₃₀ alkyl anhydride)₁₋₁₀₀,(C₈₋₅₀ aryl anhydride)₁₋₁₀₀, (C₉₋₆₀ alkylaryl anhydride)₁₋₁₀₀, (C₉₋₆₀arylalkyl anhydride)₁₋₁₀₀, (C₂₋₃₀ alkyl carbonate)₁₋₁₀₀, (C₇₋₅₀ arylcarbonate)₁₋₁₀₀, (C₈₋₆₀ alkylaryl carbonate)₁₋₁₀₀, (C₈₋₆₀ arylalkylcarbonate)₁₋₁₀₀, —R₁—O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkylether, C₆₋₄₀ aryl ether, C₇₋₆₀ alkylaryl ether, or C₇₋₆₀ arylalkylether)₁₋₁₀₀, —R₁—O—CO—NH—(R₂ or Ar—R₂ —Ar)—NH—CO—O(C₂₋₅₀ alkyl ester,C₇₋₆₀ aryl ester, C₈₋₇₀ alkylaryl ester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀,—R₁—C—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ arylether, C₇₋₆₀ alkylaryl ether, or C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, —CO—NH—(R₂or Ar—R₂—Ar)—NH—CO—O—, —R₁ —O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—(C₂₋₅₀alkyl ester, C₇₋₆₀ aryl ester, C₈₋₇₀ alkylaryl ester, or C₈₋₇₀ arylalkylester)₁₋₁₀₀, —R₃—O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—, —R₁, —NH—CO—NH—(R₂or Ar—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ aryl ether, C₇₋₆₀alkylaryl ether, or C₇₋₆₀ arylalkyl ether) ₁₋₁₀₀, —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₂₋₅₀ alkyl ester, C₇₋₆₀ aryl ester, C₈₋₇₀ alkylarylester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀, —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—O—(C₁₋₃₀ alkyl ether, C₆₋₄₀ aryl ether, C₇₋₆₀ alkylarylether, or C₇₋₆₀ arylalkyl ether)₁₋₁₀₀, —CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—,—R₁—NH—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—(C₂₋₅₀ alkyl ester, C₇₋₆₀ arylester, C₈₋₇₀ alkylaryl ester, or C₈₋₇₀ arylalkyl ester)₁₋₁₀₀,—R₃—O—CO—NH—(R₂ or Ar—R₂—Ar)—NH—CO—O—, —R₁—O—CO—NH—(R₂ orAr—R₂—Ar)—NH—CO—NH—(C₂₋₅₀ alkyl amide, C₇₋₆₀ aryl amide, C₈₋₇₀ alkylarylamide, or C₈₋₇₀ arylalkyl amide)₁₋₁₀₀, or —R₁—NH—CO—NH—(R₂ orAr—R₂—Ar)NH—CO—NH—(C₂₋₅₀ alkyl amide, C₇₋₆₀ aryl amide, C₈₋₇₀ alkylarylamide, or C₈₋₇₀ arylalkyl amide)₁ ₋₁₀₀; each Z, independently, is -M-D,wherein each M, independently, is —R—, —R—Ar—, —Ar—R—, or —Ar—; and eachD, independently, is —OH, —SH, —NH₂, —NHOH, —SO₃H, —OSO₃H, —COOH,—CONH₂, —CO—NH—NH₂, —CH(NH₂)—COOH, —P(OH)₃, —PO(OH)₂, —O—PO(OH)₂,—O—PO(OH)—O—PO(OH)₂, —O—PO(O)—O—CH₂CH₂NH₃ ⁺, -glycoside, —OCH₃,—O—CH₂—(CHOH)₄—CH₂₄—CH, —O—CH₂—(CHOH)₂—CHOH, —C₆ H₃(OH)₂, —NH₃ ⁺, —N⁺HR_(b)R_(c), or N⁺HR_(b)R_(c)R_(d); wherein each of R, R₁, R₂, R₃,R_(a), R_(b), R_(c), and R_(d) independently, is C₁₋₃₀ alkyl, each Ar,independently, is aryl.
 2. The organically-functionalized carbonnanocapsule as claimed in claim 1, wherein the diameter of a carbonnanocapsule is 3-100 nm.
 3. The organically-functionalized carbonnanocapsule as claimed in claim 1, wherein n is 1-100,000.
 4. Theorganically-functionalized carbon nanocapsule as claimed in claim 1,wherein the carbon nanocapsule is functionalized by a redox reaction. 5.The organically-functionalized carbon nanocapsule as claimed in claim 1,wherein the carbon nanocapsule is functionalized by a cycloadditionreaction.
 6. The organically-functionalized carbon nanocapsule asclaimed in claim 1, wherein the carbon nanocapsule is functionalized bya radical addition reaction.